The year was 1990-something. It was a simpler time, a happier time; a time when America still meant something. People listened to Chumbawamba on objects called "compact discs." Kids played video games instead of rotting their brains with books about Hunger Games. In this climate of boundless optimism, I became a bicycle messenger.

Back then if you wanted a job or an apartment or an adulterous liaison you had to scan the classifieds in an actual paper newspaper. So I grabbed a copy of the Village Voice and found an ad that said something like "Bicycle Messengers Wanted—Must Have Own Bike." Not only did I have a bike, but I also knew how to ride it, so as far as I was concerned I was overqualified.

Nevertheless, the next morning my stomach felt like it could grind coffee beans as I headed over the Brooklyn Bridge and into Manhattan. I arrived at the address in the ad and clomped my way up the stairs, past a sweatshop, and into a big office where dispatchers barked orders into radios, and where a handful of prospective couriers and I would be officially orientated. Basically, orientation involved the following:

• There was talk about how easily I could die. (As a New York City cyclist, I already knew this.)

• There was talk about how easily my bicycle could get stolen. (As a New York City cyclist, I already knew this, too)

• There was a lengthy speech about two hypothetical messengers that seemed to come straight from one of those 1950s hygiene films. Messenger A rode safely and intelligently and listened to his dispatcher. He made lots and lots of money, married a model, and went on to become the President of the United States. Messenger B rode like an idiot, got hit by a truck, and died.

By lunchtime, I had a clipboard with the company's logo on it (deducted from my still-theoretical wages), a laminated map of the city (also deducted), an introduction to my dispatcher as well as his blond dreadlocks (that one was free), and my first pickup at some loft on Lafayette Street.

Over the course of my six-month-long delivery career, I learned that many things I'd heard about messengers aren't true. I'll dispel some of the myths here.

Messengers Are Crazy If you watch any of those Lucas Brunelle videos you might think that being a bike messenger in New York is a nonstop thrill ride filled with danger and death, but I didn't find that to be the case—at least no more so than everyday New York riding. Then again, this may be because I rode more like Messenger A than Messenger B, savoring the meditative process of weaving through traffic and filling and disgorging my bag. I did have one accident, when a truck stopped short in front of me. I hit the bumper, did a neat little endo, and hit the rear door with my head. Then my rear wheel landed, the truck started moving again, and I resumed riding without so much as dabbing a foot. I'm sure I looked exactly like one of those drinking-bird executive desk toys.

Messenger Life Is Gritty To me the defining element of being a New York City bicycle messenger was not the grit but the glamour, and I was afforded a view of life in various rarefied social strata that few people get to experience. I delivered a bottle of wine to Francis Ford Coppola at the Pierre Hotel. I visited Oscar de la Renta's townhouse. I schlepped something to Roberta Flack at the Dakota. I flitted between fashion designers and modeling agencies as frequently as a Vogue editor or a drug dealer. I even got to make deliveries to my former workplace, where I lorded my freedom and casual attire over my erstwhile colleagues as if I'd just gotten the corner office.

Messengers Don't Make Much Money Messengers don't make any money. At least I didn't. Sure, I received a paycheck every week, but I also got my bike stolen. That put me deep into the red, and in an overall accounting, I must have ended up paying for the privilege of riding my bike all day for a living, which of course prepared me well for my next phase: amateur bike racer. By the way, if you ever ride your bike in New York City, avoid locking your bike to the leg of a mailbox, because a determined thief can actually lift one off the sidewalk.